


peggin whiskey

by vee_djarin



Category: Kingsman (Movies)
Genre: Anal Fingering, Anal Sex, Butt Plugs, Edgeplay, Female Reader, I Wrote This Instead of Sleeping, Orgasm Denial, Pegging, Plot What Plot/Porn Without Plot, Praise Kink, Smut, Strap-Ons, bottom whiskey, fluff if you squint, pure sin
Language: English
Status: Completed
Published: 2021-03-16
Updated: 2021-03-16
Packaged: 2021-03-24 20:21:30
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 2,265
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/30077808
Author URL: https://archiveofourown.org/users/vee_djarin/pseuds/vee_djarin
Summary: peggin whiskey. pretty straight forward... with some edging
Relationships: Jack | Whiskey (Kingsman)/Reader
Comments: 2
Kudos: 12





	peggin whiskey

Nothing could have prepared you for when Jack 'Agent Whiskey' Daniels asked you if you knew anything about pegging. You did know about pegging. It was something a couple of your ex boyfriends let you do. You enjoyed bringing your men such pleasure and taking good care of them. So it came as a surprise that Jack was the first to bring it up. 

"It's fine if you don't want to. I'll understand," he says dejectedly. 

"No no no no no, Jack. I would love to. I didn't tell you this before but it wouldn't be my first time. I'll take such good care of you. I promise." You take his face in your hands, caressing his cheek. 

His eyes light up, "Really? I've never done it before so I'm nervous." 

"We'll do this together. We'll go slow. I'll get everything we'll need," you reassured him. 

After he leaves the room, you get your laptop and order everything you'll need. You needed to get new toys just for Jack. You wanted to make this the absolute best for him. The website says the items will be delivered within a couple weeks. So you wait. 

.  
.  
.  
The package with his new toys arrives while he is at work. Now you have everything, you're ready to pleasure him in a way he's never been pleasured before. 

As soon as you hear the keys jingle in the door, your heart is pounding furiously with anticipation.

He walks up to you to give you his daily after work kiss. He never failed to show you how much he loves you. 

“Remember when we talked about pegging?” you asked him. 

“Yes, I do,” he says hesitantly. He was confused because the conversation was weeks ago and you hadn't brought it up until now. 

“Well I got everything we need now so we can do it whenever you want.”

Jack’s expression is dark and full of desire,“I’m free all night, darling. All yours.”

“I like that. How about we take this to the bedroom?” you suggested. 

“I like the way you think, sugar.” 

The two of you raced up the stairs and into the bedroom. As soon as you are past the threshold, both of you are stripping, discarding your clothes on the floor. His lips are on yours and your naked body is pressed against his. Your hands roam his body until they eventually tug at his soft brown hair, slowly pushing him into subspace. He moans into your mouth and you know that he is ready.

"Onto the bed. On your hands and knees," you command.

He nods and gets onto the bed and you groan at the sight. 

"Fuck, you look so good baby," you groan, rubbing a hand on his ass. 

He shudders underneath your touch. You massage his ass, making him relax. Once you decide that he is ready, you uncap the lube and pour some in your hand. He flinches as your thumb circles his hole. 

"You ready?" You ask him. 

"Yes," he gasps. 

You push your index finger slowly into him. 

"How does it feel?" 

“Not the best but it's not the worst I've felt. Very peculiar.” 

"I expected that. How about now?" You curl your finger inside him, stimulating his prostate. 

"Fuck fuck fuck fuck," he says, his speech much less eloquent than normal. 

He lets out choked gasps as your finger curls inside his tight ass. 

You reach around him and grab his cock, stroking it gently. You can tell he is close so you pull out your finger and turn him over and straddle him. 

"You're not going to cum. Not until I get to fuck you. I am going to edge you for days until you are ready for my cock. Understand?" 

"Yes ma'am." 

.  
.  
. 

It's the second night of training Whiskey to be pegged. Tonight you would use two fingers and also bring in a toy. 

This time you have him lay on his stomach, with a pillow positioning his ass higher. 

You spread the lube directly onto his asshole, pressing your index finger in easily. 

"That's such a good boy. Learning how to take my finger already," you praised. As a second finger entered him he let out a long, low groan. 

"Feels... so good," his words slur together. He pushes his ass back onto your finger. 

"That's such a dirty boy. Fucking yourself on my hand." 

You increase your pace, working until your fingers move in and out of him smoothly. Just as he is about to cum you remove your fingers. 

"I've got something else for you. I'm going to give you a safe word just in case. If you need me to stop just say 'kennedy' and I will. To make sure you understand I'm going to ask, what's the safe word, sweet boy?" 

"Kennedy." 

"Good. I'll start you off small tonight and go bigger tomorrow and the day after." You take out the 3 butt plugs you got for him. 

"I'll let you look at the sizes before we start." You set them next to him. As he examines the toys, you spread more lube onto his ass. 

"Hand me the first one." 

He hands it back to you. 

"Now, I need you to spread your cheeks for me." 

He hesitates then reaching back and pulling his cheeks apart, exposing his virgin hole. 

You slide it up and down, slicking up the lube spread all over his ass. You press the tip of the plug in gently then pull it out, teasing him. You continue teasing his hole with the plug until he is begging. 

"Please just put it in. I've been such a good boy," his whines sound absolutely helpless and its music to your ears. 

"You have been such a good boy for me." You press the plug all the way in. You do not miss the satisfactory sigh he lets out, "I think you're done tonight. Put your clothes back on. I'll have dinner ready downstairs in a half hour," you give him a final slap on the ass before going to wash off your hands so you can make dinner. 

.  
.  
. 

Tonight you are working Whiskey up to the final plug size. He has been so good with the other two so you also have another surprise for him. 

"Before we get this final plug inside you, I've got a gift for you cowboy," you say stroking his thighs. Jack is currently bent over the edge of the bed, his feet shoulder length apart. You grab one of the other toys you bought for him. 

"What's your safeword?" you ask, letting him know that you will be trying something new. 

"Kennedy." 

"Good boy." 

You squirt some lube onto the toy and slowly press it into Jack. It's not nearly as girthy as the plugs but it is specifically designed to stimulate the prostate. Jack moans and it is the most sinful sound you have ever heard. You slowly pump the toy in and out of him and when you no longer feel resistance you turn the vibrator on its lowest setting. Jack's whines become ten times louder as the toy vibrates against his prostate. Deep inside, Jack knew that when you finally made him cum while you fucked him, it would be the most mind blowing orgasm of his life. He hasn't cum in days and this is the best he's ever felt in his life. 

"Mmm Jackie baby, I love the sounds you make for me. Who would have known this is what it takes to make you fall apart?" you purred. 

"I did, I knew you'd treat me so good," he gasped. 

.  
.  
. 

Jack could not wait to get home. Tonight you would finally fuck him and make him cum. He has never trusted anyone the way he trusts you. The last few days had him very vulnerable in the bedroom but he has come to really like the vulnerability. He likes the feeling of submitting to you. Almost as much as he likes the idea of fucking you senseless but that fantasy will have to wait. 

He's been hard all day just thinking about how you will tease him and draw out his orgasm as long as possible. A tingle runs down his spine at the thought of his back being absolutely broken after tonight. 

It felt like an eternity but eventually the time came for him to return home to you. He did not even watch his speed as he drove home. 

As soon as he steps through the door you push him back against the door and press your lips to his. His hands fall to your hips as you grind against him. 

“I've been, mmr hhnf, been thinking about you all day,” he moans in between your kisses. 

“Well then. I’d hate to keep you waiting, cowboy. Let's take this rodeo upstairs.”

You kiss and pull and drag each other up the stairs. Both of you can feel the anticipation and lust hanging in the air. 

You feel Whiskey tugging at your shirt, “Nuh uh cowboy, I'll be undressing myself, but not until you're ready for me.”

He practically whimpers at your words. You palm his erection through his pants, “Now let's get these clothes off of you.”

His clothes are off his body in record time and he leans in to reconnect your lips. 

You dodge his kisses and step away to lay down a sheet on top of your comforter and a pillow at the edge of the bed.

“Hands and knees,” you order. 

Whiskey crawls onto the bed and gets into position. You spread some lube onto your fingers, rubbing it between your fingers to warm it up. When you feel the lube has warmed you gently pull the plug from his ass and replace it with two of your fingers. You pump your fingers in and out of him. Once you decide he is relaxed enough you move on to the next part. You pull out your fingers and leave to wash your hands and retrieve your strap. 

“Stay here. I'll be right back, cowboy.”

“I want you laying on your back on the edge of the bed. The pillow is going to be underneath your lower back. It's going to angle you and it's more comfortable for both of us,” you said as you reentered.

He lays down, shimmying to get comfortable. 

“One more thing.” 

He lifts an eyebrow. 

“Hands above your head,” you instructed. 

He smirked, knowing you were about to do to him what he has done to you so many times. 

“Can’t have you touching yourself. That would ruin the fun.”

You first tied his wrists together, checked if they were too tight, then tied one end of a rope to his restraints and the other to the headboard. 

“Are you comfortable?” you asked. 

“Yes ma'am.”

You strip out of your clothes and Jack eyes the devil red lingerie set you are wearing. 

“Like what you see? Too bad you can’t touch,” you teased. 

You put on the harness then tighten to straps to make sure it is stable then positioned yourself between his thighs.

“Oh darling, you got me more excited than an astronaut on the moon,” he smirks.

You push his thighs toward his chest and rub circles onto his thighs, watching as he shivered under your touch. Squirting some lube onto the dildo, you spread it around with your hand. After deciding it was lubricated enough you slowly press into him, loving the whimpers he let out. You stilled once you were fully inside him. Your hand wraps around his cock, stroking it. You started off at a slow, lazy pace. One of your hands rests on his thigh while the other pumps his cock. 

“Please more,” he gasps.

“You want more, baby? Want me to fuck you harder?”

“Yes!”

You pull all the way out, except for the tip then thrust back in. Jack’s quick breathy moans make your pussy throb. Just as his moans begin to subside you begin to thrust again. You fuck him fast but not too hard and hold his thighs to keep him in place. He yanks against the restraints, wanting to touch something. Or at least grasp the sheets. 

He was whining like never before and you knew he was close. You stroke his cock again, rubbing your thumb over the head. You pull out again and slowly pump back into him, angling up slightly so you were rubbing against his prostate, slowly coaxing out his orgasm.

Whiskey could feel the orgasm start in his toes as it ran its way all the way up his body. It was like a fire spreading across his torso. His eyes rolled back as he came, his hands balled into fists. This was twice the intensity of any orgasm he has ever had in his life. 

“That's such a good boy. Wish you could see yourself right now.” 

He looked an absolute blissful mess. 

You pull out and untie him. He stays there, completely incapacitated. You take off the strap and disassemble it, tossing it in the bathroom sink to be cleaned later and wash your hands. When you get back to the bedroom, Jack has settled into bed, waiting for you to join him. 

He sighed as you got into the bed and snuggles next to him. 

“Thank you,” he whispers. 

“You're welcome baby. I'll give you everything you ever want. All you have to do is ask”

“I just want you,” he says and presses a kiss to your head.

**Author's Note:**

> if there are spelling/grammar/continuity errors i deeply apologized. my dumbass could proof ready this 9834 times and there would still be errors. but i hope you still enjoyed.


End file.
